I will almost guarantee some update will break shit at the most inconvenient time humanly possible and the people you’ve done this for will need your help, all at the same time.

Well, yeah. That’s life as an admin under the best circumstances. There’s a running list of Windows ticking time bombs over on r/sysadmin. There are lots of good reasons to ditch Windows, but I wouldn’t say the risk of MS shutting down technically unsupported hardware is one of them (because I don’t agree it’s a substantial risk).